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A feature in the works for JDK 8 is repeating annotations:
JEP 120: Repeating Annotations
which requires making changes to javac to support the new language feature.
17 tests: http://hg.openjdk.java.net/jdk8/tl/langtools/file/250f0acf880c/test/tools/javac/annotations/repeatingAnnotations
Link to changesets:
A fine idea.